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President Barack Obama huddled with President Hamid Karzai in Chicago on Sunday, urging Afghanistan’s leader to accelerate negotiations with the Taliban over a political solution to the longest war in America’s history. But the prospect for Karzai negotiating successfully with the insurgents is clouded by a question raised by Josef Stalin, on the eve of World War II, in response to the suggestion that he offer concessions to the Pope: “How many divisions does he have?” The Taliban now ask the same question about Karzai. And should the Afghan leader also ask himself the question, he might reach a similarly dispiriting conclusion. Karzai’s independent power base is minimal, as is his ability to influence the outcome of his country’s civil war absent direct U.S. involvement. And that gives neither Karzai nor the Taliban much incentive to cut a deal with the other.

While acknowledging “hard days ahead,” Obama was painting a picture of the “Afghan war as we understand it (being) over” after the U.S. combat role ends in 2014 and Afghanistan entering a “transformational decade of peace and stability and development.” But his commander on the ground offered a more chilling assessment on Sunday. “I don’t want to, again, understate the challenge that we have ahead of us,” Gen. John Allen, commander of NATO’s ISAF mission in Afghanistan, told a media briefing on the sidelines of the NATO summit in Chicago on Sunday. “The Taliban is still a resilient and capable opponent in the battle space. There’s no end of combat before the end of 2014. And, in fact, the Taliban will oppose the ANSF (Afghan National Security Forces) after 2014.”

In other words, the war won’t end with NATO withdrawal.

It’s the realization that the Taliban will remain very much alive and kicking after NATO leaves that has prompted Obama to press upon Karzai the need to engage with greater urgency in reconciliation talks with the Taliban — and also to implement electoral reforms to diminish corruption and make elections more transparent. But Karzai is a survivor by instinct, and neither electoral reform nor serious talks with the Taliban do much to enhance his prospects of political survival.

The only thing keeping him in power over the past decade has been the presence of tens of thousands of Western troops. Even if the Afghan security forces NATO is frantically training to take over — and suffering almost weekly “green on blue” fatalities as Afghan security men turn their guns on their Western mentors — were up to par, it requires a vast leap of faith to imagine they’ll be loyal to Karzai. The President has a minimal political base; he was propelled into power as the preferred option of the U.S.-led invasion force, a candidate who had strong clan roots in the Pashtun heartland but was able to win the consent of the Northern Alliance — the Tajik, Uzbek and Hazara warlords who had been the greatest beneficiaries of the NATO intervention and comprised its key allies among Afghan fighting forces.

Since then, he has kept power by fancy footwork at the nexus of forces more powerful than himself, painting himself as the least-worst option, with the corruption and cronyism that Western leaders complain about being a symptom of that power equation, and of longstanding traditions. After all, when the CIA had first sent its operatives into Afghanistan to initiate the toppling of the Taliban, they were armed not with stirring calls to freedom and democracy, but with suitcases containing millions of dollars in hard cash. Karzai knows the limits of the loyalty of those presently aligned with the status quo, and the traditional fluidity of Afghan warlord politics. He holds his present position only because there’s no obvious alternative to play the role he’s been playing.

Neither Karzai’s rule nor the Afghan national security forces are based on a genuine national political consensus; Afghanistan remains riddled with the same deep ethnic political fissures that plagued it before the Americans arrived, and it’s highly unlikely that the Afghan security forces will somehow set themselves apart from that conflict. On the contrary, it may be no more than wishful thinking to cast the security forces as loyal to an idea of Afghanistan independent of the civil war taking place in the country. A highly plausible scenario would see those security forces break down along the ethnic fissures that correspond to the battle lines of the civil war (although there may be plenty of political infighting among Pashtuns, too), rather than one in which they remain loyal to Karzai or whomever is elected to replace him in 2014.

The Pansjiri Tajiks of the Northern Alliance, which has long provided a key part of the ranks and officer corps of the Afghan security forces, are reportedly opposed to any power-sharing deal with the Taliban, and are widely rumored to be arming themselves for a post-NATO showdown. That creates significant pressure on Karzai to put the brakes on any negotiations with the insurgents. So, as much as NATO needs Karzai to be talking to the Taliban to ease the departure of Western troops, his best interests may lie in keeping Western troops involved in propping him up for as long as possible, even if the domestic political reality facing his Western backers obliges him to embrace the 2014 strategy. (Polls find that more than two-thirds of Americans now oppose U.S. involvement in Afghanistan.)

The Taliban, for its part, also sees the limits of Karzai’s power, and brands him a “puppet” of the West. The purpose of Obama’s Afghan “surge” that began in the summer of 2009 was to double down the U.S. military commitment in order to pummel the Taliban into suing for peace and delivering it to the table sufficiently bloodied as to be ready to accept U.S. terms — including a recognition of the constitutional order put in place after the NATO invasion, and by extension the authority and legitimacy of President Karzai. But that, quite simply, has not happened, as Allen pointed out.

Feeling the wind at its back, and sensing that the tide of Afghan public opinion has turned more sharply against the presence of Western troops and that the Western powers have lost their appetite for an expeditionary war in which they’ve essentially been spinning their wheels for the past five years, the Taliban broke off secret negotiations earlier this year. The movement is reportedly split over whether to seek a compromise solution when NATO is already moving towards the exit, and hard-liners may have gained the upper hand. Pakistan retains considerable influence over a movement that was once its protege, and it is determined to see that its interests — which include having a friendly government in Kabul (Karzai is viewed by Pakistan’s security establishment as tightly aligned with India) — are accommodated in any settlement. The Obama Administration failed to even get Pakistan to agree to a deal ahead of the Chicago summit to reopen supply lines to NATO forces in Afghanistan through Pakistani territory; the supply lines have been closed since a border incident in which Western warplanes killed Pakistani troops. An accord on the future of Afghanistan clearly remains some way off.

Then there are the more militant Taliban elements that retain ties with al-Qaeda, as well as some of the movement’s younger, more embittered mid-level commanders, none of whom see any good coming out of negotiating a compromise when their primary enemy, the U.S. and its NATO partners, has made clear it intends to withdraw by the end of 2014. It’s hard to argue, in the Taliban’s internal debate, that time is not on the insurgents’ side.

And resistance to negotiation and compromise on each side of the Karzai-Taliban equation simply reinforces the same on the opposing side. So, while Obama and other NATO leaders would like to see Afghanistan’s power players adopt a narrative that allows Western forces to withdraw with a sense of having put the country on the road to peace and stability, the Afghan players seem to have other ideas. They’re not going to make this easy.

Tony Karon is a senior editor at TIME, where he has covered international conflicts in the Middle East, Asia, and the Balkans since 1997. A native of South Africa, he now resides with his family in Brooklyn, New York.